Ethoxyacetic acid → HCID 54707959, compound

HRID 1700107Notes

Reaction equation

HRID 1700107 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[OH:8][C:9]1[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)=[C:18]([CH3:19])[C:13]=2[O:12][C:11](=[O:27])[CH:10]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:3][CH2:4][C:5]([C:10]1[C:11](=[O:27])[O:12][C:13]2[C:18]([CH3:19])=[C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[CH:16]=[CH:15][C:14]=2[C:9]=1[OH:8])=[O:7])[CH3:2]

Participants

6

Reactant 3

HCID 12301Ethoxyacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54707956HCID 54707956, compound

Product 1

HCID 54707959HCID 54707959, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.21 ml of ethoxy acetic acid is added to a solution containing 5.00 g of 4-hydroxy-8-methyl-7-[(tetrahydro-2H-pyran-2-yl) oxy]-2H-1-benzopyran-2-one, 7.30 g of 4-dimethylaminopyridine and 3.816 g of N-(3-dimethylaminopropyl)- N′-ethylcarbodiimide hydrochloride. This mixture is agitated for 16 hours at ambient temperature. After diluting with dichloromethane, washing is carried out with an aqueous solution of sodium dihydrogen phosphate then with brine. After drying over magnesium sulphate, filtering and evaporating to dryness, the product obtained is triturated in a hexane-ethyl acetate mixture (4-1). The product obtained is separated and dried. In this way 5.40 g of sought product is obtained.

Workup

  1. washwashing
  2. dry with materialAfter drying over magnesium sulphate
  3. filtrationfiltering
  4. customevaporating to dryness
  5. customthe product obtained
  6. customis triturated in a hexane-ethyl acetate mixture (4-1)
  7. customThe product obtained
  8. customis separated
  9. customdried

Sources & evidence

ORD record
ord-72053edfa17a41f49dc91805cc786170
Source dataset
uspto-grants-2002_02
Patent number
US06350733B1

Reaction notes

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